The data isn’t lost, and also in talking to the expert on this he says that even if there are two entitlements for the same product, for the same email address, the user should see the models. An easy example problem case its where two people assign Shop to you, you get to see thee models based on your email address, and not based on who assigned Shop.
Another common case is where one admin person places two orders for Pro. In both cases the seat is assigned to them, and in the management page they appear twice in the members list. Both of those seats can be assigned to other people.
So far the cases I’ve figured out ended up involving two email addresses, often because the user tested Free with their personal email, loved it so much that the company brought Shop for their work email.
One imperfection I know about is that the Trimble Connect sign in isn’t synchronized to the Free or Shop sign in. You could have been using Shop with your work account yesterday, sign in to Trimble Connect with your personal email today, wonder where your models have gone to, click to start modeling, and suddenly your models are back. The reverse of that could happen too. The reason is because the app remembers what email you used the last session, and doesn’t let the Trimble Connect sign in email override that.
Dave’s incognito test would help to track down that issue, because you would be forced to sign in again.